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Unfortunately, I am in RMD and IRMAA territory but am doing my best to account for that.  Most of what you say makes sense to me except the following:   I agree. That's been my approach. I.e. selling shares not subject to the NUA until the value of the remaining shares is equal to the Gross Distribution on the 1099-R. At that point one can decide when to sell and report the sale as an NUA.    ... which I find totally confusing.  You indicate you agree with me but, at the same time, this answer seems to suggest if you sell only a certain subset of the shares, that you can, at least for the current tax year, avoid NII tax.  What do you mean by "selling shares not subject to the NUA".  For simplicity, assume there have been no share purchases or sales since the movement date to the taxable account and no dividend reinvestment and that your MAGI is high enough that you are already subject to NII tax.   The only variable when you sell some or all of those shares is the value of the shares when you sell versus the value of the shares on the movement date.  Actually, it may be simpler to just talk about the share price (assuming no splits/etc).  Do you agree that, if the share price is higher now when you are considering selling some or all of those shares than it was on the movement date, that you will owe some NII tax and that whatever you are referring to in the bold-fonted answer is irrelevant?   Thanks for all your help!

@mylittlecoins , if you were using the on-line 2024 version ,  yes amending is possible.  But for 2023, I believe you have to ask the customer service  for help or buy  ( from Intuit) and install the 2023  download version before you can amend the 2023 filed return.   Because you mention  SSN of the "kids",  I am wondering  about your tax home -- is it US or abroad ?  Just curious.

@DonnaBear65 ,  (a) Which country are you from  and when did you enter with H-1B ?   (b) The work that you did for your home-country employer  -- was it done here in the USA or while you were physically in your home country ? (c) What is/was the basis of the dispute ? What we need to determine is the sourcing country for the delayed payment and hence the questions. Generally IRS position is that the sourcing of income is where the actual work is performed. There is also the concept of "nexus".  And of course some of these categorization may be influenced by any in-effect  Tax Treaty between the US and that country.   I will circler back once I hear from you --yes ?

@onyxrubyrose30 , while my colleague @xmasbaby0  has provided you with an excellent response and included  a number of references,  I just wanted to complete this  reading list with  something from the IRS --------------> About Form W-9, Request for Taxpayer Identification Number and Certification | Internal Revenue Service.   This covers  the current form and instructions thereof.  The form itself also covers a lot of the instructions on how to fill out the form.   The assumption here is that you are a US person ( citizen/GreenCard/Resident for Tax purposes ) and that your actual work  ( for this income stream) is actually performed in the US.

No.    How to prepare 1099 & W2 https://ttlc.intuit.com/community/forms/help/how-do-i-create-w-2-and-1099-forms-in-turbotax/00/25869 You need to give a 1099NEC to anyone you paid $600 or more to for the year. But not to corporations or for merchandise. You send the IRS a copy of the 1099NEC with the transmittal summary form 1096. These are due to the person by Jan 31 and to the IRS by Jan 31 also. You can prepare W2 and 1099NEC & 1099MISC in either the Desktop Home & Business program or the Online Premium version using the QEF Quick Employer Forms.

The W-9that you fill out and send back to TikTok will be used by TikTok to issue a tax document  (most likely a 1099NEC) to you  in January for the income you have received for whatever you are doing to generate income from them.   That income will be self-employment income.   If you have had even $400 of self-employment income, you are required to enter it on your tax return and pay self-employment tax for Social Security and Medicare.   If you have self-employment income for which you will pay self-employment tax for Social Security and Medicare,  you will need to use online Premium software or any version of the desktop software download so that you can prepare a Schedule C for your business expenses.     https://ttlc.intuit.com/community/self-employed/help/how-do-i-report-income-from-self-employment/00/26653   https://ttlc.intuit.com/community/self-employed/help/what-is-the-self-employment-tax/00/25922   https://ttlc.intuit.com/turbotax-support/en-us/help-article/import-export-data-files/enter-self-employment-business-expenses-like-home/L1k6HJY4A_US_en_US?uid=m6jrthmp     If you live in a state with a state income tax, you might need to make estimated payments to your state.   https://turbotax.intuit.com/tax-tips/small-business-taxes/the-home-office-deduction/L1RZyYxzv https://ttlc.intuit.com/turbotax-support/en-us/help-article/estimated-taxes/make-estimated-tax-payments/L5svMESaC_US_en_US?uid=mdna5aoh     https://turbotax.intuit.com/tax-tools/calculators/self-employed/   https://ttlc.intuit.com/community/business-taxes/discussion/self-employed-don-t-miss-these-tax-moves/00/3400413     https://ttlc.intuit.com/turbotax-support/en-us/help-article/import-export-data-files/enter-schedule-c/L5Fz3j5us_US_en_US?uid=m6a6gknk   https://ttlc.intuit.com/turbotax-support/en-us/help-article/payroll-additions-deductions/qualify-qualified-business-income-deduction/L0rM2cIIQ_US_en_US?uid=m5zpoxad   https://ttlc.intuit.com/turbotax-support/en-us/help-article/self-employment-taxes/self-employed-expenses-deduct/L37ZS1B8T_US_en_US?uid=m6fntpg7  

Where to find the License Code https://ttlc.intuit.com/community/tax-topics/help/i-can-t-find-my-license-code/01/852973 Amazon how to download and install your software order https://www.amazon.com/gp/help/customer/display.html?nodeId=G2CJPY7HHXBLMR5E To get the License Code from Amazon, One user said...... I was just having this same issue, but I just figured it out. So I thought I'd share in case you are still looking for an answer. Go to Your Account; then Digital Games and Software (under Digital Content and Devices section at the bottom middle); your TurboTax purchase should show there under Downloads and Codes; the license code will be the 16 digit code next to "Activation Key". Hope this helps!

Turbo Tax will automatically give you the 1040SR if you or your spouse is 65 or older. It is exactly the same as the regular 1040, just bigger type so it goes on 4 pages instead of 2. The Standard Deduction Chart is on page 4.   In the Online version you don't get a choice which one to use. If you are using the Desktop program and look at it in Forms Mode it shows the 1040 but if you print it out it will be the 1040SR. There is a way to force the one you want in the Desktop program.

The Form 1040 and Form 1040SR are identical except for the size of the print.  All of the lines are the same, and all of the calculations of your tax due or refund are the same.   If one or both of you are 65 or older, when you use TurboTax software the return will print out on a Form 1040SR.   You do not need to worry one bit that your refund or tax due will be affected by using 1040 or 1040SR.

If any 8949 shows the mail-in option, during e-File TurboTax Online will ask for a PDF of your transaction details.   Last I heard, TurboTax download version did not. Maybe it's better this year.  

What products?  Did you buy the Desktop program?  Did you pay for it?   Did you  get an email with the License Code?  Log into your Intuit account and see if it is waiting for you to download it.     Where to find the License Code https://ttlc.intuit.com/community/tax-topics/help/i-can-t-find-my-license-code/01/852973 How to get started with the Desktop program, install and activate it https://ttlc.intuit.com/turbotax-support/en-us/help-article/product-delivery/download-software-turbotax-com/L7u9oLEkq_US_en_US?uid=luqgvzrd    Otherwise How to contact Turbo Tax https://ttlc.intuit.com/community/using-turbotax/help/how-do-i-contact-turbotax/00/26991

I'll give this a try: It is my understanding that, when you sell any of that company stock, you pay capital gains on the profit over the cost.  I agree   The profit that is over the equal to that amount that you had when you did the NUA (in your case in 2007) is subject to LTCG I think you are saying over the amount is subject to LTCG. If so, Yes, assuming there is a gain. There could be a loss.   but exempt from NII Yes, but... I think that makes things too complicated. My approach has been to sell shares until the value left equals the Gross Distribution Amount on the 1099-R. If my MAGI income triggers the NIIT for that tax year, that is the price one has to pay.   and the profit above that is ALSO subject to capital gains (possibly STCG if there is reinvested dividends less than a year old, otherwise LTCG) and IS subject to NII.  I agree.   In other words, if you sell at a higher price than what it was priced at when you moved the shares to a taxable account, I think you must pay some NII on it (assuming your MAGI triggers NII, of course). I agree. If my MAGI income triggers the NIIT for that tax year, that is the price one has to pay.   I do not believe you can avoid NII completely if the price has appreciated since when the NUA occurred.  I agree.   The way I read what you are saying leads me to think that you think you can avoid the NII perhaps until some year when your MAGI would drop enough so as to moot the NII I agree. That's been my approach. I.e. selling shares not subject to the NUA until the value of the remaining shares is equal to the Gross Distribution on the 1099-R. At that point one can decide when to sell and report the sale as an NUA.   Separately: In your case, you mentioned pro-rating sales and pro-rating the NUA. I forgot to mention that you also would have to pro-rate the NUA on the Worksheet for Form 8960. Also, assuming you know about the IRRMA tax brackets if you are on Medicare. I.e. the added premium for Parts B and Parts D at different income levels. Passing from one income level to the next can trigger a nasty surprise since the brackets are not progressive.   Another recommendation: If you have a IRA and you are not yet 73 and on Medicare, distribute the IRA funds prior to having to 73 which triggers RMD's. RMD's raise havoc with tax planning.